I'm surprised to see the opposition to self-signed certificates from the EFF. Pushing people towards centralized certificate authorities seems to be anti-freedom. Maybe there is a decentralized approach instead.
If there aren't major technical obstacles we might be willing to take pull requests for STARTTLS Everywhere that allow mailservers to announce self-signing policies, but it hasn't been a priority thus far because LE certs are so easy to get and are slightly more authenticated.